UNLABELLED: Background/ Objectives: Surgical residency is widely recognized as a highly stressful phase due to long working hours and the challenges of managing complex cases. Additionally, family responsibilities, such as being a spouse or parent, can have a positive or negative impact on residents' well-being. This study aimed to explore the relationship between clinical supervision and mental well-being among otolaryngology residents in Saudi Arabia, focusing on how supervision conditions influence well-being at different stages of training. METHODS: This was an analytical cross-sectional correlational study conducted among Saudi otolaryngology head and neck surgery residents. An online survey was used to collect data from 64 residents, utilizing the Dutch Residents Educational Climate Test (D-RECT) to assess clinical supervision and the Warwick-Edinburgh Mental Well-being Scale (WEMWBS) to measure well-being. The data were analyzed to determine the association between supervision conditions and well-being across different residency levels. RESULTS: The results showed that the majority of residents reported higher mean scores for items such as "I've been feeling useful" (3.53 ± 1.23), "I've been feeling interested in new things" (3.28 ± 1.13), and "I've been dealing with problems well" (3.27 ± 1.10). No statistically significant difference in overall WEMWBS scores was found between junior and senior residents. However, mental well-being was significantly associated with all four D-RECT domains (supervision, feedback, coaching assessment, and consultant attitude), with a positive correlation observed between clinical supervision and well-being. CONCLUSIONS: This study highlights the critical role of clinical supervision in supporting the mental well-being of otolaryngology residents. Enhanced supervision practices, particularly those emphasizing constructive feedback and supportive consultant attitudes, could mitigate burnout and improve resident outcomes. These findings underscore the need for targeted interventions in residency programs to promote well-being and optimize the learning environment.